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1
Wash the maple leaves with warm water and pat dry on paper towels. Line several cookie sheets with wax paper. Place the orange candy, green candy, and milk chocolate melting wafers into separate microwavable bowls. Microwave each bowl separately, stirring occasionally, until the candy is smooth, about 1 minute. Using a small, clean craft brush or your fingertip, paint spots in the 3 different colors of melted candy in an even layer (not too thin) over the top side of each leaf. While the candy is still wet, swirl the colors slightly to blend. Place the leaf on one of the cookie sheets, coated side up. Repeat with the remaining leaves. If the candy becomes too thick, reheat in the microwave for several seconds, stirring frequently. Place the cookie sheets in the refrigerator until the candy is set, about 5 minutes.
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2
Carefully peel the leaves from the hardened candy. They come off surprisingly easily. Use a toothpick or clean tweezers to remove any small pieces of leaf that may remain. (The leaves and other candy pieces can be made up to 5 days in advance, covered, and kept in a cool dry place.)
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3
Line a cookie sheet with wax paper. Spoon the remaining milk chocolate into a small bowl to use for the acorn tops. Soften 4 or 5 caramels at a time in the microwave for 3 to 4 seconds. Roll each caramel into an acorn (egg) shape. Place the chocolate jimmies in a small shallow bowl. Reheat the milk chocolate in the microwave, stirring often, until smooth, about 10 seconds. Dip the large end of an acorn caramel into the melted chocolate to cover about 1/4 inch. Allow any excess chocolate to drip off. While the acorn is still wet, dip the chocolate end into the jimmies to coat. Transfer to the cookie sheet. Repeat with the remaining acorns. Refrigerate until set, about 5 minutes.
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4
Spoon 1/4 cup of the chocolate frosting into a ziplock bag, press out the excess air, and seal. Spread the tops of the cupcakes with the remaining chocolate frosting and smooth. Arrange the cupcakes in pairs to make a circle on a large platter.
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5
Gently press the leaves into the frosting on the cupcakes, overlapping them. The leaves on the edge of the right half of the wreath will sweep to the right, while those on the left half will sweep to the left. Place the acorns randomly over the cupcakes. Snip a 1/8-inch corner from the bag with the chocolate frosting and pipe a dot of frosting at the top of each acorn to make a stem.
